The paper compares the two dukes in Shakespeare's Measure for Measure and The Tempest as they pull the strings in advance the plot in their respective play. Prospero, the exiled Duke of Milan, lords over an enchanted island in The Tempest, and Vincentio, who dons a disguise to be able to walk around his city unnoticed, rules Vienna in Measure for Measure. The tactics that the authority figures, Vincentio and Prospero, employ in order to maintain or regain their power and influence are examined in the context of prevalent cultural and political conditions in Jacobean England. Since the paper argues that Prospero's and Vincentio's power is reflected in their clothing in a society notoriously divisive on the basis of social status, they need to resort to disguising themselves to blend in. By doing so, they gain firsthand knowledge about the information which would otherwise be unavailable to them. This increased level of omniscience results in a series of decisions by the dukes who display a rather flawed understanding of justice and mercy. The primary goal is to punish the characters who participated in the act of transference of power opposite the dukes: Vincentio's deputy Angelo who proved himself to be corrupt and hypocritical, and Prospero's brother Antonio who ended up usurping his throne. Both dukes approach to disciplining the offenders is by staging a punishment spectacle. The stage-management, manipulation and deceit exhibited by both dukes are linked to Shakespeare's own theatrical practices and, in the case of Prospero, as a possible self-referential farewell letter before his retirement. Both plays are underlined by a complicated system of reflections which double, triple, and subvert the plot by using the lower class characters when necessary. This serves to emphasize the theatricality of royal life and the complete arbitrariness of justice in some cases.